Antispasmodic compound and process of producing the same



Fatented lder; i, ldzd.

ran s rata earns \VKLLIAIM H. ENGELS, GE RAHWAY, NEW JERSEY, ASSIGNQR TO 'MEBICK ,& 00., OF

NEW YQRK, N. Y., A CORPORATION OF NEW YORK.

ANTHEPASKODEC COHPOUND AND PROQESS 0F PRODUCING THE SAME.

Z-l'o Drawing. fiz'iginal application filed April 25, 1922, Serial No. 55,6,424. Divided filed May 13, 1922. Serial No. 560,720.

To all whom it may concern:

Be it known that 1,,WILL1AM H. ENonLs, a citizen of the Republic of Germany, and a resident of ltahway, in the county of Union and State of New Jersey, have invented certain new and useful Improvements in Antispasmodic Compounds and Processes of lroducing the Same of which the following .is a specincation.

Although benzyl sulfuric acid, benzyl phosphoric acid," tenzyl succinic acid and ch mical literature as laboratory products Fbeilstein ll, 1056; ll. Erna, pp. 638

slid i048; Beric to, 35, p. 4078?, none of them has, so far as I know, received any in dustrial application, and particularly none in the therapeutic art.

So far as I know, inthe only benzylesters which have heretofore received any industrial or thera ,eutic application (e. g., benzylbenzoate, enzylcinnamate, dibensylsuccinate, benzylsalicylate, and others), the acid group has been fully saturated by the benzyl group or groups, and a heretofore insurmountable obstacle to their use hypodermically has been their insolubilityin water, in consequence of which their therapeutic use has been substantially limited to administration per os.

lhave' produced, for the first time, benzylester compounds and, specifically, alkali benzyl succinates, especially sodium benzyl succinate, of a Water-solubility and purity compatible with hypodermic, intravenous and subcutaneous use, and a process by which they may be obtained, and I believe that l. have not merely converted certain d substances into products or" great I, but have greatly enlarged the medicnally important field of antispasmodic remedies.

lily invention also involves the discovery the conditions under which any by-products that maybe present with the unsaturated benzyl succinate are eliminated at the time that the ester is transformed into heated .to about 80, neutralized with anhyoenzyl pliilialic acid have been mentioned in and this application application Serial No. 556,424, which was filed in the United States Patent Office on or about April 25, 1922.

To explain one method by which my invention may be carried out, the following example is given: y

l kilogram succinic acid monobensylester is. dissolved in 4 litres alcohol 7 (92-95%),

drous sodium carbonate and filtered hot.

Gn cooling, the sodium monobenzylsuccinate crystallizesout and may be recovered from the mother liquor in the customary way.

It will be observed that in the illustrative example, the process is carried out under anhydrous conditions. This is to enable this step to accomplish the dualfunction'of producing therapeutic purity as well as watersolubility, the by-products, if any, present with the ester being retained in the acetone or alcohol solvent.

In the illustrative example of my process, I have mentioned sodium carbonate as the neutralizing compound. It will be understood, however, that other alkali compounds, such, for exam is, as ammonium, potassium or lithium car onates or hydroxides are to be considered as equivalents.

What I claim and desire to secure. by Let ters Patent of the United States is:

-l. As an antispasmodic adapted 'for hypo- ,dermic injection, a therapeutically pure' alkali benzyl succinate.

' E. Games,

53. W. Huimsssrzorr. 

